4-amino-3,4-dihydro-2H-naphthalen-1-one;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A sample of 26.55 g. of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride is dissolved in 250 ml. water and a solution of 21.8 g. of potassium cyanate in 75 ml. of water added. The reaction mixture is stirred for 72 hours, the precipitate formed in the reaction is collected by filtration and dried to afford 21.45 g. of the title compound, m.p. 225° C. (dec.). the precipitate formed in the reaction is collected by filtration dried to afford 21.45 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g. of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml. of 95% ethanol and 214 ml. of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried by adding ethanol and evaporating the mixture in vacuo. This procedure affords 20.2 of the title compound, melting point 200°-216° C. (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried by adding ethanol evaporating the mixture in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The following formula I 1,2,3,4-tetrahydro-4-oxo-1-naphthylurea compounds are prepared by reacting 1,2,3,4-tetrahydro-4-oxo-1-naphthylisocyanate or isothiocyanate with the appropriately substituted amines, or by reacting 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride with the appropriately substituted isocyanates, isothiocyanates or carbamoyl chlorides by the process of Example 6. The compounds obtained are listed in Table I below. The compounds obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 10 g of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride in 200 ml of dry tetrahydrofuran (THF) under a nitrogen atmosphere, 76 ml of triethylamine is added dropwise. The mixture is stirred for an additional 5 minutes, and 3 ml of methylisocyanate is added dropwise. The reaction mixture is stirred for 1 hour at room temperature and the solid collected. The filter cake is washed with THF and then with 3 × 50 ml of water. The THF filtrate is concentrated in vacuo to afford some product. The water-insoluble solid is air dried to afford 8.8 g of the title compound melting point 219°-221° C. Recrystallization from about 150 ml of methanol yeilds 7.4 g of the above product, melting point 220°-223° C. The reaction mixture is stirred for 1 hour at room temperature the solid collected The filter cake is washed with THF The THF filtrate is concentrated in vacuo to afford some product dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-formyl-1,2,3,4-tetrahydro-4-oxo-1-naphthylamine in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200°-216° C (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200° C to 216° C (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200° C to 216° C (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200° C to 216° C (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200° C. to 216° C. (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml of 95% ethanol and 214 ml of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried using ethanol to remove water in vacuo and this procedure affords 20.2 g of the title compound, melting point 200° C. to 216° C. (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried to remove water in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A sample of 26.55 g. of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride is dissolved in 250 ml. water and a solution of 21.8 g. of potassium cyanate in 75 ml. of water added. The reaction mixture is stirred for 72 hours, the precipitate formed in the reaction is collected by filtration and dried to afford 21.45 g. of the title compound, m.p. 225° C. (dec.). the precipitate formed in the reaction is collected by filtration dried to afford 21.45 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 19.6 g. of N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)formamide in 214 ml. of 95% ethanol and 214 ml. of 2N hydrochloric acid is heated at reflux for 3 hours and then stirred at room temperature for 2 days. The solution is filtered and the filtrate concentrated in vacuo to afford a dark residue. The residue is dried by adding ethanol and evaporating the mixture in vacuo. This procedure affords 20.2 of the title compound, melting point 200°-216° C. (dec.). at reflux for 3 hours The solution is filtered the filtrate concentrated in vacuo to afford a dark residue The residue is dried by adding ethanol evaporating the mixture in vacuo